1394241-70-3

Basic information

• Product Name: C₁₇H₁₄N₂O₄S
• Synonyms: C₁₇H₁₄N₂O₄S
• CAS NO: 1394241-70-3
• Molecular Weight: 342.375
• Mol File: 1394241-70-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₁₇H₁₄N₂O₄S(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₇H₁₄N₂O₄S(1394241-70-3)
• EPA Substance Registry System: C₁₇H₁₄N₂O₄S(1394241-70-3)

Safety Data

• Hazardous Substances Data: 1394241-70-3(Hazardous Substances Data)

Upstream product

• 4025-64-3 3-Carboxybenzenesulfonyl chloride 
• 149355-52-2 7-cyano-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 1394241-64-5 C₁₇H₁₅N₅O₄S 

Relevant articles and documents

3-(3,4-dihydroisoquinolin-2(1 H)-ylsulfonyl)benzoic acids: Highly potent and selective inhibitors of the type 5 17-β-hydroxysteroid dehydrogenase AKR1C3

A high-throughput screen identified 3-(3,4-dihydroisoquinolin-2(1H)- ylsulfonyl)benzoic acid as a novel, highly potent (low nM), and isoform-selective (1500-fold) inhibitor of aldo-keto reductase AKR1C3: a target of interest in both breast and prostate cancer. Crystal structure studies showed that the carboxylate group occupies the oxyanion hole in the enzyme, while the sulfonamide provides the correct twist to allow the dihydroisoquinoline to bind in an adjacent hydrophobic pocket. SAR studies around this lead showed that the positioning of the carboxylate was critical, although it could be substituted by acid isosteres and amides. Small substituents on the dihydroisoquinoline gave improvements in potency. A set of reverse sulfonamides showed a 12-fold preference for the R stereoisomer. The compounds showed good cellular potency, as measured by inhibition of AKR1C3 metabolism of a known dinitrobenzamide substrate, with a broad rank order between enzymic and cellular activity, but amide analogues were more effective than predicted by the cellular assay.